Asymmetric synthesis via chiral silicon reagents. Chiral α-hydroxyalkyl anion equivalents from vinylsilanes containing optically active amino or alkoxy groups on silicon

Chiral vinylsilanes containing optically active functional groups on silicon have been used as precursors for chiral α-hydroxyalkyl anion equivalents via a sequence of addition of η-butyllithium, coupling with organic halides, and oxidative cleavage of the silicon-carbon bond, to give optically active alcohols of up to 60% ee.